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A Review for Biological Activity on Hydrazide Hydrazones: a Promising Moiety

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A Review for Biological Activity on Hydrazide Hydrazones: a Promising Moiety European Journal of Molecular & Clinical Medicine ISSN No-2515-8260 Volume 07, Issue 03 2020 A Review For Biological Activity On Hydrazide Hydrazones: A Promising Moiety Shalini K Shah*1, Anju Goyal2 1Research scholar, Bhupal Nobel’s University, Udaipur, Rajasthan. 313001, India. 2 Bhupal Nobel’s University, Faculty of Pharmacy, Udaipur, Rajasthan. 313001, India. CORRESPONDENCE: [email protected] Khyati College of Pharmacy, Plot no 116, Palodia, Sheelaj, Ahmedabad, Gujarat Abstract: Hydrazide-hydrazones derivatives are available in numerous bioactive atoms and show a wide variety of biological activities, like antibacterial, antitubercular, antifungal, anticancer, mitigating, anticonvulsant, antiviral and antiprotozoal activity. In this manner numerous researchers synthesised different hydrazide-hydrazones and assess them for their activity. This paper is centred on the overview of the literature finding of the last 15 years covering the research on antimicrobial, anticancer and anticonvulsant of hydrazide-hydrazones derivatives. Keywords: Hydrazide-hydrazones, antibacterial, anticonvulsant, anticancer. Introduction: Hydrazide-hydrazones a carbonyl category with azomethine group (-NH-H=CH-) is very popular moiety in last two decade’s for research because of its play a vital role in the research work as intermediate. This is the very interesting topic for the researcher due to their wide verity of promising biological activities including anti-microbial, anti-cancer1-4, anti-conversant, anti-tubercular5-8, anti- inflammatory9,10 analgesic activities11-12. The basic structure of hydrazones having two nitrogen (- NNH2) and one carbon (C=O) atoms which make C=N bond by conjugation of a lone pair of electrons of nitrogen. They are showing both nucleophilic as well as electrophilic nature for activity. The general method for the synthesis of the hydrazones is the reaction of hydrazine with carbonyl compounds such as aldehydes or ketones in solvents like ethanol, methanol, butanol. In this case some hydrazide-hydrazone components have been considered as drugs and have been used in clinics, such as furazolidone13, Nifuroxazide,(D) an oral antibiotic; used in colitis and enteritis caused by bacteria or protozoan infections, treatment respectively, Nitrofurazone14in the treatment of skin infections due to skin grafts and nitrofurantoin15 in urinary infections. (Fig.1) A B 857 European Journal of Molecular & Clinical Medicine ISSN No-2515-8260 Volume 07, Issue 03 2020 C D Fig. 1 Chemical structure of medicines containing hydrazide-hydrazone moiety: nitrofurazone (A), nitrofurantion (B) and furazolidone (C) Antibacterial Activity: The multi- resistant bacterial strains property of bacteria increase the searching of effective and non-toxic agents for new researchers. Even some drug (mentioned previously) are used with compromised immune system of patients. So the scopes of hydrazide- hydrazones showed promising result with less side effects. In this series Łukasz Popiołek et al. in 2019 synthesised 19 new compounds of hydrazide-hydrazones of 5-nitrofuran-2-carboxylic acid. The condensation processed with various aliphatic and aromatic aldehydes gave these new series with antibacterial activity and then compare that with vitro antimicrobial assays. This research showed the substitution of alkyl chains showed higher activity against Gram-negative bacteria than hydrazones with aryl substituents. The substitutions also showed anti-fungal activity. Researcher found by structure-activity analysis that short alkyl chains are good for activity like compound no. 1,2,3,4 and 5.16(Fig 2 and table 1) Fig 2: 5-nitrofuran-2-carboxylic acid hydrazide-hydrazones derivatives. Table no -1: Derivatives of 5-nitrofuran-2-carboxylic acid hydrazide-hydrazones Compound no R 1 2 3 4 5 6 2-iodophenyl 858 European Journal of Molecular & Clinical Medicine ISSN No-2515-8260 Volume 07, Issue 03 2020 The compound 6 which contain 2-iodophenyl substituent, were showed highest minimal fungicidal concentrations against all reference Candida spp. In 2019 an another scientist Van Hien Pham et al. have been synthesized hydrazide- hydrazones with 1-adamantane carbonyl moiety with various substituted benzaldehyde and acetophenones. The new synthesized compounds were tested for activities against some Gram-negative and Gram-positive bacteria, and the fungus Candida albicans. Compound 7,8,9,10 (Fig 3) showed potent activity for antibacterial against Gram-positive bacteria such as Enterococcus faecalis (ATCC13124), Staphylococcus aureus (ATCC25923), and Bacillus cereus (ATCC 13245).17 Fig 3: Hydrazide-hydrazones with 1-adamantane carbonyl Table no-2: Results of Hydrazide-hydrazones with 1-adamantane carbonyl derivatives Comp. R1 R2 Minimum inhibitory concentration (MIC) in µM No Enterococcus faecalis Staphylococcus aureus Bacillus cereus 7 H -OH 12.5 12.5 12.5 8 H -NO2 25 25 25 9 CH3 -OH 12.5 25 25 10 CH3 -NO2 12.5 50 100 STD: Streptomycine 350 350 175 In 2018 one more scientist Samir Y Abbas and his team synthesized some quinoxaline N- propionic and O-propionic hydrazide derivatives as antibacterial agent for different bacterial strains. In that they found compound no 13 showed fourfold potency against bacterial strains for A. fumigatus (table no 2) and compound 12 and 11 showed two fould and equipotent activity for various strain against gentamycin as standard drug. The values of Minimum inhibitory concentration in µg/mL are summarized in Table no. 2. The study of quinoxaline N- propionic hydrazide derivative (fig 4) showed that Changing the substituent on pyrazole from phenyl to 4-chlorophenyl to 4- methylphenyl (11→12→13) had a moderate difference in the antimicrobial activity. The 3-p-tolyl-pyrazolyl is responsible for this in case of compound 13.18 Fig no. 4: Propanoic acid derivative 859 European Journal of Molecular & Clinical Medicine ISSN No-2515-8260 Volume 07, Issue 03 2020 Table No. 3 Results of Propanoic acid derivative Comp. no Ar S.aureus S.epidermidis S.pyogenes B. E.faecalis subtilis 11 C6H5 29.9 27.6 28.5 34.8 23.8 12 C6H4Cl4 29.2 26.1 28.3 36.3 23.6 13 C6H4(CH3)4 30.0 28.2 28.5 32.9 26.4 Std: Gentamycin Łukasz Popiołek et al. in 2017 obtained a series of hydrazide hydrazones of 2,3-disubstituted propionic acid by the using ethyl ester and in second step hydrazide-hydrazones were obtained by condensation reaction of appropriate hydrazide with various aromatic and hetero-aromatic aldehydes (fig 5). And all the compounds tested for the antimicrobial activity against Gram positive like S. aureus S. epidermidis , B. subtilis, B. cereus, Micrococcus luteus and Gram-negative bacteria B. bronchiseptica, E. coli, Klebsiella pneumoniae, Proteus mirabilis, S. typhimurium, P. aeruginosa. But the 2-3- dibromo propionic acid were showed good activity against all in comparison of other derivative. These compound also tested for anti-fungal activity where fungi belonging to yeasts (Candida albicans ATCC 10231, Candida parapsilosis ATCC 22019). They are showed good to moderate activity.19 Compound 14 Fig 5: new hydrazide-hydrazones of 2,3-dihalogen (Br and Cl) substituted propionic acids as compound 14 The in vitro screening result of newly synthesized (E)-N’-1(substituted benzylidene) benzohydrazides moiety revealed that some of the compounds had significant antimicrobial activity by G. Thirunarayanan et. al in 2017. They synthesized ten newly benzohydrazide by the reaction of appropriate mixture of benzohydrazide and ortho, meta and para substituted benzaldehydes with sodiumhydroxide solution in ethanol as a solvent. The antibacterial activity measured by zone of inhibition in mm values and all the benzohydrazide derivatives have been showed satisfactory sensitivity against M. luteus bacterial strain except 2-chloro and 3-hydroxy substituents.20 X= H, 3-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 4-C H3, 2-NO2, 3-NO2 Compound 15 Fig 6: benzohydrazide showing interesting activity against all used bacterial strains. 860 European Journal of Molecular & Clinical Medicine ISSN No-2515-8260 Volume 07, Issue 03 2020 Dommati et al. in 2016 obtained novel 14 new benzohydrazide derivatives by using vanilline as starting material and evaluated them for in vitro antibacterial activity. The highest activity showed by compound 15 and 16 (fig 7)against two Gram-negative bacteria, (E.coil (ZOI=24, 22) and P. aeruginosa ZOI= 20,18) and Gram positive (S.aureus ZOI= 25, 20 and S.pyrogenes ZOI= 18, 16) bacterial strain by using control as Norfloxacin at 50µg/mL.21 16 17 Fig 7: benzohydrazide derivatives Where as in 2016 Lukasz Popiolek and Anna Biernasiuk synthesized another series of hydrazide- hydrazones of phenylacetic and hydroxyacetic acid by the condensation reaction of 2-substituted acetic acid hydrazide with different aromatic aldehydes (fig 8). All synthesised compounds were screened for antimicrobial and anti-fungal activity by using the broth microdilution method. In this series they found one compound very strong activity against all tested reference Gram positive bacteria with B. subtilis, even 32 and 16 times more than standard drug cefuroxime and ampicillin respectively. Whereas the activity against B. cereus was 8 times higher than activity of cefuroxime for the same compound 18. 22 Fig 8: substituted acetic acid hydrazide Compound 18 In 2016 Madhusudan Raju et al. synthesized and evaluated antimicrobial activity for N-substituted-1- benzyl-1H-1,2,3triazole-carbohydrazide derivatives (fig 9). Four out of ten newly synthesized compounds showed significant antimicrobial activity
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